Novel Photosensitizer Based on Bacteriopurpurinimide and Magnetite Nanoparticles

Suvorov, Nikita; Grin, M. A.; Popkov, Alexander M.; Garanina, Anastasiia S.; Mironov, A. F.; Majouga, Alexander G.

doi:10.6060/mhc160645s

Cited by 4 publications

(1 citation statement)

References 11 publications

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“…Therefore, versatile and convenient synthetic approaches are relevant for the construction of such molecules with enhanced spectral and photophysical properties, activity, and selectivity as well as for the achievement of an appropriate lipophilicity/hydrophilicity ratio. Nanostructural PSs can be used to solve this issue, resulting in an enhanced penetration and loading into the tumor mass due to their effective extravasation from defect neovasculature. − The mechanism of action of some thiol-containing compounds is directly associated with their tendency to be reversibly oxidized in the presence of GSH. Considering the photodynamic effect as the main contributing factor to initiate the oxidation of crucial cellular components by reactive oxygen spices (ROS) changes in redox intracellular state via GSH interaction with the molecules containing disulfide groups significantly contribute to the light induced phototoxicity to cancer cells .…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Investigation of Photophysical and Biological Properties of Novel S-Containing Bacteriopurpurinimides

Mironov¹,

Grin²,

Pantushenko³

et al. 2017

J. Med. Chem.

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Novel hybrid molecule containing 2-mercaptoethylamine was synthesized starting from O-propyloxime-N-propoxy bacteriopurpurinimide (dipropoxy-BPI), which was readily oxidized in oxygen atmosphere yielding the corresponding disulfide analogue (disulfide-BPI). Spectral, photophysical, photodynamic, and biological properties of compound were properly evaluated. Compounds bearing disulfide moiety can directly interact with glutathione (GSH), thereby reducing its intracellular concentration. Indeed, mice sarcoma S37 cell line was treated in vitro with disulfide-BPI, yielding a CC value of 0.05 ± 0.005 μM. A relatively high level of singlet oxygen was detected. It was demonstrated (by fluorescence) that the PS was rapidly accumulated in a cancer nest (S37) at a relatively high level after 2 h upon intravenous administration. After 24 h, no traces of the molecule were detected in the tumor mass. Moreover, high photodynamic efficiency was demonstrated at doses of 150-300 J/cm against two different in vivo tumor models, achieving 100% regression of cancer growth.

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